CHAPTER FOUR
All was quiet at Pirate Cay. Spring break for most colleges was ending, and the other students had left a few days ago on the helicopter to St. Francis to be flown back to the mainland, large checks in their hot little hands to compensate them for their suffering on the island and the entertainment they had provide for him and his guests. All in exchange, of course for an iron-clad, non-disclosure agreement that would oblige them to return the money along with anything else they managed to earn after graduation if they ever breathed a word about their time on Pirate Cay.
Tara couldn’t help envying them just a bit for the lesser quality of their genetic endowment compared to hers, which allowed them to leave the island. Cursed with the “right” DNA, she was forced to remain on Pirate Cay to produce his heir, which was now the main, if not sole, purpose in her new life of servitude.
Then, this morning, Kelly had departed on the same helicopter on some mission or other, whose goal she hadn’t seen fit to share with Tara and Delia. Not that Tara missed her. It was clear that she was not pleased that he had chosen Tara instead of her for this project. Kelly had been nasty enough before, and Tara could only imagine what she would do to her now if she got the chance.
So, she and Delia were basically alone here now with just their employer and the local staff, with very little to do. Of course, there was the beach and the pool, but, as lovely as they were, one could only spend so many hours sunbathing and swimming. There was the gym, which they could use whenever he wasn’t in there, but, despite their promise to him after their losing the pony cart race so shamefully that they would use the Pitcher College gym paid for by his generous donations, they were content to wait for their return home to keep that vow.
The usual distractions of normal life were not available to them. Only he and Kelly had internet access. Their contact with the outside world was limited to composing cheery emails to their families a couple of times a week to reassure them that they were having a great time, emails that he had to approve before they were sent.
Their phones were useless, as the nearest cell tower on another island was out of range and only he had access to the satellite link.
The biggest excitement was when the doctor, a very attractive Indian American woman in her mid thirties, came once a day to take Tara’s temperature in order to chart her fertility cycle. Not that she shared any information; she simply nodded, entered the number and said that she’d be back tomorrow.
On the bright side, their backs and butts had healed almost completely from being whipped by Robert, the muscular, Black flogger as the well-deserved punishment for their miserable performance in the pony cart race.
All in all, Tara wasn’t sure how she would handle nine months of this. It was better than being flogged or made to provide sexual favors to a gaggle of horny hedge funders, but it made Professor Tremayne’s terminally dull Econ 102 lectures seem positively scintillating. Talk about the dismal science!
Nevertheless, our Two Musketeers made the best of it. Early that afternoon, they lay poolside on lounge chairs under a large umbrella, clothed, if one could call it that, in one of the micro string bikinis that Kelly had selected for them. Their employer had been closeted in his office all morning, working on some deal or other and he had gone back in there right after lunch.
They had at least found some reading material lying around in the great room. Delia was reading a potboiler detective novel about a pair of New York City detectives who seemed to spend more time bantering with each other, indulging in BDSM and fucking than solving crimes. Tara was leafing aimlessly through a magazine which spent a lot of time speculating over which celebrities were a couple these days. Since it was three months out of date, most of them were probably already split up and paired with someone else by now.
Tara heard the copter first and looked up. “I wonder if that’s Kelly coming back,” she speculated. But as it drew nearer, she could tell that it wasn’t their employer’s copter. No, this craft belonged to the Providencia Coast Guard, which could mean only one thing-they were about to be visited by Sir Freddy Bascome, Big Fred, the Prime Minister of this lovely island paradise.
“Shit!” Delia exclaimed, knowing that this would likely mean that she would be called upon to pleasure Big Fred, who had taken a real shine to her for some unfathomable reason, though likely her large breasts were part of the picture. The copter circled the compound and touched down on the landing pad, which was out of their view.
They were left alone for a half hour or so, while Big Fred transacted whatever business he needed to do with their employer, probably, Tara surmised, collecting a cash payment for allowing the goings on at Pirate Cay to proceed unmolested by his police forces.
But soon enough they emerged, dressed casually in shorts and polo shirts and installed themselves at a table near the two students. One of the local girls trailed behind them carrying a pitcher of what looked to be ice-cold margaritas and some glasses, which she set down on the table before disappearing silently back into the house.
The two men sat talking quietly, glancing over at the Tara and Delia, but not inviting them to join them. Tara felt a chill run down her spine. No doubt, they were planning some activity that would likely be more fun for them than it would be for the two students.
Finally, their employer looked hard in their direction. “Tara, Delia, come here!” he ordered. They put their reading material down, got up and hustled to stand in front of the two men.
“Take those suits off,” he ordered. “I want to see how you’re healing.”
‘Not that the suits cover much,’ Tara thought, though she hastened to comply, as did Delia.
“Turn around,” he commanded. The girls did a slow pirouette.
“Come closer”. They approached. The men looked them up and down like a rancher eyeing stock at a cattle auction.
“I think they’ve healed well, don’t you Big Fred,” he opined.
“Oh, my, yes. That cream your doctor has is like a miracle. They’re just luscious, aren’t they?”
Their employer shook his head. “Yes, they look good on the outside, but what’s inside matters, doesn’t it?”
“Certainly,” the PM replied.
“Have you girls been going to the gym?” their employer asked.
“No, sir,” they replied in unison. Tara knew this meant trouble.
“You do remember that you promised to get in shape, to use the gym I provided for you at Pitcher?”
“Yes, sir,” Delia replied. “And we will, as soon as we get back there.”
“Is there something wrong with the gym here?”
“No, sir,” Tara replied. She knew this was not going well.
“Tara, if you are going to bear my heir, you need to be in tip-top shape. And I expect you to do the same Delia, to provide your friend with motivation.”
“Understood, sir,” Tara said. “We’ll go to the gym right now and start working out.” She started to turn to gather her suit and head there.
“I can’t trust you lazy sluts to do a proper workout on your own,” he replied. “You need a personal trainer and I have just the man for the job.” He pressed a button on his phone.
As though he had been waiting for the call, Robert, the flogger, stepped through the glass doors and into the pool area, striding forcefully towards the two women. He was dressed in a tank top that showed off his bulging arm and chest muscles, sweat pants and running shoes. He carried a riding crop almost the length of his arm that began with a cloth-wrapped handle and ended with a rather nasty looking tongue.
“Robert tells me he was a drill Sergeant in the Royal Providencia Marines before he came to work for me.”
“Indeed he was! One of the best!” the PM confirmed. “I used to review the troops he had drilled and they were always perfect.”
Robert smiled and bowed slightly. “Thank you Mr. Prime Minister. I’m honored to have served our country.” He turned to the boss. “How may I be of service?”
“Robert, I want you to take charge of these two lazy whores and whip them into shape like you did the rawest of raw recruits back in the Marines.” Tara shuddered at the word “whip”, with which she had little doubt had been meant literally.
“With pleasure, boss,” Robert replied, an evil grin on his face. Then, he turned to face Tara and Delia. “Alright, you worthless cunts, let’s get started with some stretches to loosen those flabby muscles of yours.”
The two women looked confused as to what to do next. “We’ll start with the hip abductors. Sit on your asses, legs in front of you facing the audience.” The crop in his right hand was raised, at the ready to punish any laggard behavior. They scurried into position. The concrete of the pool deck had been baked in the sun since morning and burned the still-sensitive skin of their butts and thighs.
“Now, spread those legs.” Tara did her best to comply. “Further,” Robert urged. “I want a 180˚ angle between those thighs, you hear me?”
Tara stretched mightily. So did Delia. They probably got close to the desired angle for a few seconds, but it was hard to hold the position.
She noticed their employer and the PM staring fixedly between their legs. She knew that the position stretched her pussy lips wide open. Being naked at Pirate Cay was hardly worth remarking on, but spreading herself that wide for an audience was extremely embarrassing.
Robert had them open and close their legs several times, before deciding it was time to move on. “On your feet now, move it!” he yelled. Tara scrambled to her feet. “Face me!” he shouted . She turned so that her back was to her boss and the PM.
“Now bend over and touch your toes! On the double, sluts!” She quickly complied. Nevertheless, she heard the whoosh of the crop and felt the line of fire explode across the twin globes of her ass.
“Legs further apart!” Robert shouted. Tara was going to complain that he hadn’t told them that before, but the pain had taken her breath away. She heard the crack of the crop against ass flesh again and heard Delia yelp in distress. “I said legs apart!” he shouted.
As a result of the position they had been required to hold, their butt cheeks were spread wide apart. From the feel of the air against the delicate tissue inside the crack, Tara was sure that her back passage was on full display for the audience.
Robert had them repeat the toe touches at least a dozen times.
Then he said, “OK, you bitches. Enough of the showing off. Time for some jumping jacks. You know what that is?”
“I’m not sure sir,” Delia replied.
“Turn and face the audience. I’m going to show you once and once only. Now pay close attention.” He stood legs together, arms by his side. Then, he jumped, landing with his feet apart and his arms spread out to the side. He jumped again and landed back in the original position. “You got that?”
“Yes, sir!” they both replied.
“Well, what the fuck are you waiting for?” He swung the crop, slashing it across Delia’s ass.
Tara took the hint and jumped. Delia took a moment to collect herself, before she started as well.
Tara knew that each time they jumped their naked breasts jiggled up and down. She couldn’t help seeing that their employer and Big Fred were transfixed by the sight, especially by Dee’s large breasts, which bounced wildly every time she landed.
The first several weren’t so bad. But, it was the hottest part of the day; the tropical sun was beating down on them and on the concrete from which the heat radiated upwards. The sweat was pouring down Tara’s body and she was soon panting desperately for breath.
Tara couldn’t go on any more without a rest. So she stopped. A second later she saw Robert’s arm raised and felt a line of intense pain explode across her breasts as he brought the crop down at full force on her unprotected tits.
“Did you hear me say stop?” He roared, raising the crop again.
“No sir!” she screamed in a mix of fear and agony. Drawing on every reserve of strength she had, she began another set of jumping jacks. At some point, Delia had to stop for an unauthorized rest and suffered a vicious blow across her large, pendulous breasts.
Each of them took a few more slashing blows across their tits before they got through Robert’s required number of jumps and they heard the blessed words. “Alright you sluts, take two and drink some water. We don’t want you passing out and troubling the doctor, do we?”
After an all too brief rest, Robert ordered, “Enough lazing about. Drop and give me twenty.“
Tara and Delia looked at each other, then at Robert. “I’m sorry, I don’t understand, sir? Twenty what?” Delia asked.
“Are you stupid? Twenty what? Twenty push-ups you worthless worms! Now!” he screamed. The women quickly got down and tried to do a push-up, something neither of them had done since some long-forgotten grade school gym class.
Tara sort of lifted her upper body, but her hips and legs remained on the ground. “I said push-ups! Raise the whole body! Only the hands and toss touch the ground!” He emphasized each command with a slash of the crop against one or another of the girls’ asses. They each howled in pain and collapsed.
Under the prodding of Robert’s whip, they were each eventually able to do a few of the required lifts, before collapsing in helpless exhaustion.
Robert raised the crop, ready to try to spur them on, but their employer finally called a halt. “OK, Robert, no point beating a dead whore. I think that’s all they’re going to do today no matter how much you tire your arm out. But you keep at it every day and I’ll bet they’ll be doing fifty push-ups by the end of the week and begging for more. Now give them some water and come and join us for a drink.”
The men sat and enjoyed their drinks in the shade as the two women slowly recovered. They were drenched in sweat, their hair matted against their faces, their tits and asses marked with glowing, painful red streaks.
When they had recovered enough to sit up, he asked them, “So was that a good workout?”
Tara wanted desperately to tell him off, to tell him that she wouldn’t bear his heir if she were the last woman on earth. She had to swallow hard to hold back the urge to do something that would earn her a whipping that would make the previous ones seem like a walk in the park. But she did, hoping that Delia would do the same for both of their sakes.
“Yes, sir,” she managed to say. Delia nodded agreement.
“That’s good. You’ll be in tip-top shape in no time. Now, don’t you think you should thank Robert for his efforts?”
Tara groaned inwardly at this suggestion, knowing full well what it meant. No mumbled verbal, “Thank you, Robert” would suffice. No, her gratefulness would have to be demonstrated physically in front of an audience who would have no fear of critiquing her performance. And failure to please would have painful consequences beyond a poor review. That was how it was on Pirate Cay.
She crawled towards Robert, subserviently as her employer would expect. The personal trainer stood briefly to lower his pants. Tara could see that his penis was already semi-erect in anticipation of the pleasure she would soon be providing.
He re-took his seat as she neared him, his right hand guiding her mouth to its target.
Big Fred, not one to leave all the fun for one of his constituents, stood and lowered his shorts. “Delia, my dear girl, come and show Big Fred some love”. Out of the corner of her eye, Tara saw her friend moving to fulfill his command.
The two women occupied themselves with pleasing the two island men, while their employer sat between them, content, at least for now to watch them have their fun.
Robert was the more active of the two, thrusting his hips forward, as Tara took as much of his considerable length and girth as she could into her mouth while remaining able to gulp a bit of air now and then. The PM was more passive, leaning back and letting Delia stimulate the head of his penis with her tongue.
After a while, the PM exclaimed, “Come on Delia, time to take a ride on Big Fred.” She rose and climbed onto his lap, lowering herself onto his erection. She rode slowly up and down as he fondled her tits, which were bouncing almost as much as they had when she was doing her jumping jacks.
Meanwhile, Robert was pressing Tara’s head even harder into his crotch. She could feel his leg muscles tightening as his excitement grew.
With a strained voice, Robert said, “Jerk me off on your face, girl.” This was something Tara was loath to do, but she knew better than to disobey. At least she would be able to breath with him out of her mouth.
She brought his dick next to her cheek, stroking it against her face with one hand as she moved the other up and down the shaft. “Oh, fuck, yeah,” he moaned. Tara closed her eyes as, with a loud groan, he began spurting everywhere, onto her cheek, her nose, her forehead and into her sweat-soaked hair.
“Good one, Robert!” she heard her employer exclaim. Robert’s secretions were seemingly all over her face, dripping down onto her breasts as he finally allowed her to pull away from him. Tara was disgusted with the gross mess. Most of all she was disgusted with herself for being unable to do anything besides accept this as her lot in life.
Meanwhile, the Prime Minister, turned on by his countryman’s orgasm, was approaching his own, his hands moving Delia’s body up and down on his shaft. “Yes, girl, that’s so good. Make Big Fred happy, ohh, fuck!” he exclaimed as his body went rigid with pleasure and he pulled Delia tight to his chest.
Their employer sat back in his chair and took a sip of his drink enjoying the site of his guests and his slaves in various states of exhausted disarray. “I think that session was beneficial to all, wouldn’t you agree?”
“Oh, most certainly,” Big Fred replied.
“Absolutely, sir,” Robert added. “We’ll get those two sluts in shape. Count on it.”
Tara felt compelled to nod in agreement. As she did so, another dollop of Robert’s semen dripped off her face onto her breasts.
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